Chromioenamines can be generated by treatment of O-acetyloximes with chromium(II) via two steps of one-electron reduction and successive isomerization, and the species react with aldehydes to give gamma-amino alcohols after reduction with LiAlH4.

(Diiodomethyl)trimethylsilane (Me3SiCHI2, 1) is produced by treatment of iodoform with manganese in the presence of Me3SiCl. Aldehydes are converted to (E)-1-trimethylsilyl-1-alkenes in a stereoselective manner with a geminal dichromium reagent generated from 1, manganese, Me3SiCl, and a catalytic amount of CrCl3[thf]3 in THF. Similarly, (E)-1-alkenylboronic esters are prepared stereoselectively in good to excellent yields by treatment of aldehydes with a geminal dichromium reagent derived from Cl2CHB(OR)2 [(OR)2 = OCMe2CMe2O] and LiI instead of 1.

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amino alcoholsamino alcohols (acyclic compounds) P 0130 -089Generation of Chromioenamines by Reduction of O-Acetyloximes with Chromium(II) and Their Application.-Chromioenamines are generated by treatment of O-acetyloximes with Cr(II) via two steps of one-electron reduction and successive isomerization. These species react with aldehydes to give γ-amino alcohols after reduction with LiAlH 4 . -(TAKAI,